Method of producing synthetic resins and products thereof



Patented July 11, 1933 UNITED STATES PATENT OFFICE LOUIS WEISBEBG- ANDWILLARD I. GBEENWALD, 01 NEW YORK, N. 22, ASSIGNOBS TO WEIBBEBG &GBEENWALD, 1110., 01' NEW YORK, N. Y., A GORPORA'I'ION 01 NEW YORK men0! PRODUCING SYNTHETIC amms AND PBODUGIS THEREOF I0 Drawing.

This invention relates to the production of synthetic resins.

It is the object of the invention to provide a method of producingresins and improved resin products.

The invention depends upon the reaction of triethanolamine with suitableacids under regulated conditions. Various acids may be used either aloneor in combination. For example, phthalic anhydride is a suitable acidand when combined with triethanolamine it produces a resin which issatisfactory for many uses. Other acids which may be used are, forexample, oleic, citric, tartaric, maleic, malic and fumaric. It isdesirable also to employ combinations of these acids, and particularlyto replace a part of the phthalic anh dude with one or more of thealiphatic acids since the use of these acids tends to produce tougherresins which are less brittle and less susceptible to moisture.

In carrying out the invention, we mix suitable proportions oftriethanolamine and an acid such as phthalic anhydride and heat themixture to a suitable temperature, which may vary from about 100 C.upward to 220 or 230 C. The reaction is usually conducted at atmosphericressure. If a part of the hthalic anhydride is replaced with an alipatic acid, the latter is preferably added after the phthalic anhydrideis dissolved and the temperature is reduced to prevent foaming, causedpresumably by the release of water by the reaction. The temperature maythen be raised gradually until the reaction is complete.

Although we prefer to use phthalic anhydride in part at least as theacid ingredient, other acids or mixtures thereof may be usedparticularly those aliphatic acids hereinbefore mentioned. Moreover,triethanolamine may be replaced in part by other polyhydric alcoholssuch as glycerol and glycol, which are known to react with acids to formresins.

As examples of the invention, the following will serve to illustrate thepreferred procedure:

143 parts of triethanolamine and 222 of Application filed larch 81,1981. Serial Ito. 528,700.

phthalic anhydride are heated to 150 C. After all the phthalic anhydrideis dissolved, 64 parts of citric acid are added. The tem erature is thenreduced to 110, because t ere is considerable foaming. The temperatureis gradually brought back to 150 as the foaming diminishes. The totaltime of heating is approximately two hours. The reaction can be carriedout much more ra idly at higher temperatures, but the di culty withfoaming is increased.

. Another example is as follows:

Triethanolamine, 64 parts; phthalic anhydride, 155; oleic acid, 18. Themixture is heated at 150 0., oleic acid being left out until afterreaction between the other components has taken place. The total heatingtime with this mixture is a little over an hour, the difi'erence beingdue to the fact that there is less foaming.

The reaction products are resins having properties similar to othersynthetic resins of similar character. They differ, however, in chemicalconstitution, being reaction prodnets in whole or part oftriethanolamine. These products can be employed generally in the artsfor purposes to which synthetic resins are adapted.

Various changes may be made in the procedure and materials employed inthe reaction to produce resins of varying characteristics. withoutdeparting from the invention or sacrificing any of the advantagesthereof.

We claim:

1. A synthetic resin including the reaction product of triethanolaminewith an organic carboxylic acid.

2. A synthetic resin consistin of the reaction product of triethanolammewith an organic carboxylic acid.

-A aynthetic resin including the reaction pro uct of triethanolaminewith phthalic anhydride.

4. A synthetic resin including the reaction product of triethanolaminewith plithalic anhydride, and an aliphatic carboxylic acid.

5. A synthetic resin including the reaction product of triethanolaminewith a polybasic organic carboxylic acid.

6. A synthetic resin consisting of the reion action products ofpolyhydric alcohols including triethanolamine with an organic carboxylicacid.

7. A synthetic resin consisting of the re- 5 action products ofpolyhydric alcohols in- 1 resins which comprises heating a mixture oftricthanolamine with a polyhasic organic carboxylic acid.

12. The method of producing synthetic resins which comprises heating amixture of :1 tricthanolamine with hthalic anhydride.

13. The method 0 producing synthetic resins which comprises heating amixture of triethanolamine with phthallc anhydride and an aliphaticcarhoxylic acid.

r 14. The method of producing synthetic resins which comprises heating amixture of triethanolamine with a mixture of organic carboxylic acidsincluding a polybasic acid.

15. The method of lproducing synthetic the temperature to avoid foaming,and thereafter increasing the temperature until the reaction iscomplete.

16. A synthetic resin including the reaction roducts of triethanolaminewith phthahc anhydride and an organic carboxylic acid.

17. A synthetic resin consisting of the reaction products of polyhydricalcohols including triethanolamine with phthalic anhydride and anorganic carboxylic acid.

18. A synthetic resin consisting of the reaction products oftriethanolamine with phthalic anhydride and an organic carboxylic acid.

19. The method of producing synthetic resins which comprises heating amixture of trieithanolamine with an organic carboxylic aci 20. Themethod of resins which comprises eating a mixture of polyhydric alcoholsincludin triethanolamine with an organic carboxy ic acid.

21. A synthetic resin consisting of the reaction product oftriethanolamine' and one or more acids from the roup consisting ofphthalic anhydride, oleic, citric, tartaric, maleic, malic and fumaricacids.

22. The method of roducing synthetic resins which comprises eating amixture of triethanolamine and one or more of the acids of the groupconsisting of phthalic anhydride, oleic, citric, tartaric, maleic, malicand fumaric acids.

In testimony whereof we afiix our signal-osins which comprises eatin amixture of tures. A iriothanolamine with phtha ic anhydride LOUISWEISBERG. until the phthalic anhydride is dissolved, WILLARD F. GREENWALD. adding an organic carboxylic acid, reducing DISCLAIM E R1,918,222.Lou's Weisberg and Willard F. Greenwald,

PRODUCING SYNTHETIC RESINS AND PRODUCTS Tsmnaor.

July 11, 1933. Electric Company.

Hereby said patent.

New York, N Y. Mm'mon or Patent dated Disclaimer filed October 3, 1936,by the assignee, General disclaims claims 1, 2, 3, 4, 5, 10, 11, 12, 13,14, 16, 1s, 19, 21, and 22 o [Oficial Gazette November 10, 1.936.]

roducing synthetic action products of polyhydric alcohols includingtriethanolamine with an organic carboxylic acid.

7. A synthetic resin consisting of the re- 5 action products ofpolyhydric alcohols in- 1 resins which comprises heating a mixture oftricthanolamine with a polyhasic organic carboxylic acid.

12. The method of producing synthetic resins which comprises heating amixture of :1 tricthanolamine with hthalic anhydride.

13. The method 0 producing synthetic resins which comprises heating amixture of triethanolamine with phthallc anhydride and an aliphaticcarhoxylic acid.

r 14. The method of producing synthetic resins which comprises heating amixture of triethanolamine with a mixture of organic carboxylic acidsincluding a polybasic acid.

15. The method of lproducing synthetic the temperature to avoid foaming,and thereafter increasing the temperature until the reaction iscomplete.

16. A synthetic resin including the reaction roducts of triethanolaminewith phthahc anhydride and an organic carboxylic acid.

17. A synthetic resin consisting of the reaction products of polyhydricalcohols including triethanolamine with phthalic anhydride and anorganic carboxylic acid.

18. A synthetic resin consisting of the reaction products oftriethanolamine with phthalic anhydride and an organic carboxylic acid.

19. The method of producing synthetic resins which comprises heating amixture of trieithanolamine with an organic carboxylic aci 20. Themethod of resins which comprises eating a mixture of polyhydric alcoholsincludin triethanolamine with an organic carboxy ic acid.

21. A synthetic resin consisting of the reaction product oftriethanolamine' and one or more acids from the roup consisting ofphthalic anhydride, oleic, citric, tartaric, maleic, malic and fumaricacids.

22. The method of roducing synthetic resins which comprises eating amixture of triethanolamine and one or more of the acids of the groupconsisting of phthalic anhydride, oleic, citric, tartaric, maleic, malicand fumaric acids.

In testimony whereof we afiix our signal-osins which comprises eatin amixture of tures. A iriothanolamine with phtha ic anhydride LOUISWEISBERG. until the phthalic anhydride is dissolved, WILLARD F. GREENWALD. adding an organic carboxylic acid, reducing DISCLAIM E R1,918,222.Lou's Weisberg and Willard F. Greenwald,

PRODUCING SYNTHETIC RESINS AND PRODUCTS Tsmnaor.

July 11, 1933. Electric Company.

Hereby said patent.

New York, N Y. Mm'mon or Patent dated Disclaimer filed October 3, 1936,by the assignee, General disclaims claims 1, 2, 3, 4, 5, 10, 11, 12, 13,14, 16, 1s, 19, 21, and 22 o [Oficial Gazette November 10, 1.936.]

roducing synthetic

